Potassium Hydroxide → 2-Bromo-6-[(4,6-dimethoxy-2-pyrimidinyl)thio]benzoic acid

HRID 2106967Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2106967
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([SH:11])[C:7]=1[C:8]([OH:10])=[O:9].[OH-].[K+].CS([C:18]1[N:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[N:19]=1)(=O)=O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([S:11][C:18]2[N:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[N:19]=2)[C:7]=1[C:8]([OH:10])=[O:9]

Komponenten

5

Edukt 3

HCID 14797Potassium HydroxideHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 12423631HCID 12423631, Verbindung

Produkt 1

HCID 150594242-Bromo-6-[(4,6-dimethoxy-2-pyrimidinyl)thio]benzoic acidAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

7.0 g of 6-bromothiosalicylic acid was dissolved in 20 ml of an aqueous solution of 4.0 g of potassium hydroxide, and then, 6.9 g of 2-methylsulfonyl-4,6-dimethoxypyrimidine and 20 ml of dimethylformamide were added thereto. The mixture was stirred at room temperature for one hour and poured into a large amount of ice water. The aqueous solution was washed with chloroform and then, neutralized with hydrochloric acid. An oily substance thereby released was extracted with diethyl ether. The diethyl ether layer was dried and passed through a FURORIDIL short column. Diethyl ether was distilled off under reduced pressure to obtain 3.9 g of the desired compound as white powder.

Aufarbeitung

  1. washThe aqueous solution was washed with chloroform
  2. extractionAn oily substance thereby released was extracted with diethyl ether
  3. dry with materialThe diethyl ether layer was dried
  4. distillationDiethyl ether was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f73cdf7034e646b18316253dd082b57c
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04932999

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